Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids.
Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids.
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DOI：
10.1021/acs.joc.8b00734
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发表时间：
2018-07
期刊：
影响因子：
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通讯作者：
Dong-Yun Zhao;Haofan Luo;Binhui Chen;Wenteng Chen;Guolin Zhang;Yongping Yu
中科院分区：
文献类型：
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作者：
Dong-Yun Zhao;Haofan Luo;Binhui Chen;Wenteng Chen;Guolin Zhang;Yongping Yu
我们以8-氨基喹啉为导向基团，D_2O为氘源和溶剂，发展了钯催化的H/D交换反应。该反应在芳香族酰胺的邻位C-H和脂肪族酰胺的β位C-H上实现了选择性的H/D交换。通过去除导向基团获得邻位氘代芳香酸和β-氘代脂肪酸。并提出了可能的机理。
We develop a palladium-catalyzed H/D exchange reaction with 8-aminoquinoline as the directing group as well as D2O as the source of deuterium atom and solvent. This reaction achieves selectively H/D exchange at the ortho-C-H of aromatic amides and the β-C-H of aliphatic amide. Ortho-deuterated aromatic acids and β-deuterated aliphatic acids are obtained by removal of the directing group. And a possible mechanism is also proposed.